FeCl₃-Catalyzed Nucleophilic Substitution of Propargylic Acetates with Enoxysilanes

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Abstract

An efficient FeCl₃-catalyzed substitution reaction of propargylic acetates with enoxysilanes under mild conditions to afford corresponding γ-alkynyl ketones has been developed. The substitution reaction is followed by a TsOH-catalyzed cyclization without purification of the γ-alkynyl ketone intermediates, offering a straightforward synthetic route to tri- or tetrasubstituted furans.

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This article has been cited by 6 ACS Journal articles (5 most recent appear below).

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  Aryl Aldehydes as Traceless Dielectrophiles in Bifunctional Titanocene-Catalyzed Propargylic C–X Activations

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  Organic Letters2011 13 (20), 5680-5683

  • Aryl Aldehydes as Traceless Dielectrophiles in Bifunctional Titanocene-Catalyzed Propargylic C–X Activations

    Catherine A. Campos, Joseph B. Gianino, David M. Pinkerton, and Brandon L. Ashfeld
    Organic Letters2011 13 (20), 5680-5683

    The titanocene-catalyzed construction of all-carbon substituted tertiary centers directly from aromatic aldehydes is described. The starting aldehyde behaves as a traceless functionality in the formation of multiple carbon–carbon bonds through consecutive ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Atom-Economical Chemoselective Synthesis of 1,4-Diynes and Polysubstituted Furans/Pyrroles from Propargyl Alcohols and Terminal Alkynes

  Tao Wang, Xin-liang Chen, Li Chen, and Zhuang-ping Zhan
  Organic Letters2011 Article ASAP

  • Atom-Economical Chemoselective Synthesis of 1,4-Diynes and Polysubstituted Furans/Pyrroles from Propargyl Alcohols and Terminal Alkynes

    Tao Wang, Xin-liang Chen, Li Chen, and Zhuang-ping Zhan
    Organic Letters2011 Article ASAP

    Under different conditions, the reaction of propargyl alcohols and terminal alkynes leads to the selective formation of 1,4-diynes and polysubstituted furans/pyrroles. Water is the only byproduct in the selective synthesis of 1,4-diynes and pyrroles, and ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Ytterbium(III) Triflate Catalyzed Tandem Friedel−Crafts Alkylation/Hydroarylation of Propargylic Alcohols with Phenols as an Expedient Route to Indenols

  Xiaoxiang Zhang, Wan Teng Teo and Philip Wai Hong Chan
  Organic Letters2009 11 (21), 4990-4993

  • Ytterbium(III) Triflate Catalyzed Tandem Friedel−Crafts Alkylation/Hydroarylation of Propargylic Alcohols with Phenols as an Expedient Route to Indenols

    Xiaoxiang Zhang, Wan Teng Teo and Philip Wai Hong Chan
    Organic Letters2009 11 (21), 4990-4993

    A method to prepare indenols efficiently by ytterbium(III) triflate catalyzed tandem Friedel−Crafts alkylation/hydroarylation of propargylic alcohols with phenols is described. The reaction was accomplished in moderate to excellent yields and ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Brønsted Acid-Catalyzed Propargylation/Cycloisomerization Tandem Reaction: One-Pot Synthesis of Substituted Oxazoles from Propargylic Alcohols and Amides

  Ying-ming Pan, Fei-jian Zheng, Hai-xin Lin and Zhuang-ping Zhan
  The Journal of Organic Chemistry2009 74 (8), 3148-3151

  • Brønsted Acid-Catalyzed Propargylation/Cycloisomerization Tandem Reaction: One-Pot Synthesis of Substituted Oxazoles from Propargylic Alcohols and Amides

    Ying-ming Pan, Fei-jian Zheng, Hai-xin Lin and Zhuang-ping Zhan
    The Journal of Organic Chemistry2009 74 (8), 3148-3151

    An efficient one-pot propargylation/cycloisomerization tandem process has been developed for the synthesis of substituted oxazole derivatives from propargylic alcohols and amides with use of p-toluenesulfonic acid monohydrate (PTSA) as a bifunctional ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  One-Pot Synthesis of Substituted Furans Using Cu(OTf)₂-Catalyzed Propargylation/Cycloisomerization Tandem Reaction

  Ying-ming Pan, Su-yan Zhao, Wen-hua Ji and Zhuang-ping Zhan
  Journal of Combinatorial Chemistry2009 11 (1), 103-109

  • One-Pot Synthesis of Substituted Furans Using Cu(OTf)₂-Catalyzed Propargylation/Cycloisomerization Tandem Reaction

    Ying-ming Pan, Su-yan Zhao, Wen-hua Ji and Zhuang-ping Zhan
    Journal of Combinatorial Chemistry2009 11 (1), 103-109

    A convenient one-pot propargylation/cycloisomerization tandem process has been developed for the synthesis of substituted furans derivatives from 1,3-dicarbonyl compounds and enoxysilanes with propargylic alcohols or acetates using copper(II) triflate as ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links

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